Carbanionic reactivity of the anomeric center in carbohydrates

被引:148
|
作者
Somsák, L [1 ]
机构
[1] Univ Debrecen, Dept Organ Chem, H-4010 Debrecen, Hungary
关键词
D O I
10.1021/cr980007n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthesis of the structures in synthetic and natural product chemistry was devised by changing the electrophilic character to nucleophilic at the anomeric carbon of the carbohydrates. The carbanionic character and reactions of the carbon-metal bond at the anomeric center were considered to study the stereoselective transformations among the carbohydrates. It was found that the C-glycosyl compounds and glycals were rich source of chiral, nonracemic ethers and could be used for the syntheses of biologically relevant natural and unnatural compounds.
引用
收藏
页码:81 / 135
页数:55
相关论文
共 50 条
  • [21] Specific band observed in VCD predicts the anomeric configuration of carbohydrates
    Monde, K
    Taniguchi, T
    Miura, N
    Nishimura, SI
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) : 9496 - 9497
  • [22] An alternative method for anomeric deacetylation of per-acetylated carbohydrates
    Li, YW
    Li, YX
    Wei, Z
    Guan, HS
    CHINESE JOURNAL OF CHEMISTRY, 2004, 22 (01) : 117 - 118
  • [23] Specific band observed in VCD predicts the anomeric configuration of carbohydrates
    1600, American Chemical Society, Columbus, United States (126):
  • [24] A novel and efficient deprotection of the allyl group at the anomeric oxygen of carbohydrates
    Yu, B
    Zhang, JB
    Lu, SF
    Hui, YZ
    SYNLETT, 1998, (01) : 29 - +
  • [25] A facile route for the regioselective deacetylation of peracetylated carbohydrates at anomeric position
    Chittaboina, S
    Hodges, B
    Wang, Q
    LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (01) : 35 - 38
  • [26] ANOMERIC EFFECT IN CARBOHYDRATES - AN ABINITIO STUDY ON EXTENDED MODEL SYSTEMS
    KALIANNAN, P
    VISHVESHWARA, S
    RAO, VSR
    PROCEEDINGS OF THE INDIAN ACADEMY OF SCIENCES-CHEMICAL SCIENCES, 1986, 96 (05): : 327 - 339
  • [27] ROLE OF THE ANOMERIC CENTER IN SUGAR SWEETNESS
    BIRCH, GG
    SHAMIL, S
    SHEPHERD, Z
    EXPERIENTIA, 1986, 42 (11-12): : 1232 - 1234
  • [28] Preparation and reactivity of metallated carbohydrates
    Potts, A
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U198 - U198
  • [29] CARBOHYDRATES - ASPECTS OF STRUCTURE AND REACTIVITY
    HOUGH, L
    TARELLI, E
    SCIENCE PROGRESS, 1977, 64 (256) : 569 - 592
  • [30] Gas phase spectroscopy of hydrated carbohydrates: The anomeric effect laid bare
    Simons, John P.
    Mayorkas, Nitzan
    Cocinero, Emilio J.
    Rudic, Svemir
    Gerber, R. Benny
    Davis, Benjamin G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241